(S)-2-O-benzyl-3-O-hexadecanoyl-1-O-<6-O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-gylcero-D-galacto-2-nonulopyranosylonate)-2,3,4-tri-O-acetyl-D-galactopyranosyl>glycerol

Base Information

• Chemical Name: (S)-2-O-benzyl-3-O-hexadecanoyl-1-O-<6-O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-gylcero-D-galacto-2-nonulopyranosylonate)-2,3,4-tri-O-acetyl-D-galactopyranosyl>glycerol
• CAS No.: 132929-03-4
• Molecular Formula: C₅₈H₈₇NO₂₄
• Molecular Weight: 1182.32

Synonyms:

Chemical Property of (S)-2-O-benzyl-3-O-hexadecanoyl-1-O-<6-O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-gylcero-D-galacto-2-nonulopyranosylonate)-2,3,4-tri-O-acetyl-D-galactopyranosyl>glycerol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-O-benzyl-3-O-hexadecanoyl-1-O-<6-O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-gylcero-D-galacto-2-nonulopyranosylonate)-2,3,4-tri-O-acetyl-D-galactopyranosyl>glycerol

There total 9 articles about (S)-2-O-benzyl-3-O-hexadecanoyl-1-O-<6-O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-gylcero-D-galacto-2-nonulopyranosylonate)-2,3,4-tri-O-acetyl-D-galactopyranosyl>glycerol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

benzyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside (35017-04-0) → (S)-2-O-benzyl-3-O-hexadecanoyl-1-O-<6-O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-gylcero-D-galacto-2-nonulopyranosylonate)-2,3,4-tri-O-acetyl-D-galactopyranosyl>glycerol (132929-03-4)

Guidance literature:

Multi-step reaction with 6 steps

2: H₂ / Pd(OH)2-C / methanol / 3 h / Ambient temperature

3: 79.6 percent / pyridine / 15 h / Ambient temperature

4: 65 percent / hydrazine acetate / dimethylformamide; ethyl acetate / 50 °C

5: 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / -5 °C

6: molecular sieves 4A, BF₃-Et₂O / CH₂Cl₂ / 1) -10 deg C, 2 h, 2) room temperature, 15 h

With pyridine; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium hydroxide - carbon; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1248/cpb.38.3347

Reference yield:

(S)-2-(benzyloxy)-3-hydroxypropyl acetate (109429-01-8) → (S)-2-O-benzyl-3-O-hexadecanoyl-1-O-<6-O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-gylcero-D-galacto-2-nonulopyranosylonate)-2,3,4-tri-O-acetyl-D-galactopyranosyl>glycerol (132929-03-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 72.5 percent / pyridine / 3 h / 80 °C

2: 77.4 percent / NH₄OH / methanol / 15 h / Ambient temperature

3: 85 percent / triethylamine / CH₂Cl₂ / 15 h / Ambient temperature

4: 74.6 percent / 80percent AcOH / 1 h / 80 °C

5: molecular sieves 4A, BF₃-Et₂O / CH₂Cl₂ / 1) -10 deg C, 2 h, 2) room temperature, 15 h

With pyridine; ammonium hydroxide; 4 A molecular sieve; boron trifluoride diethyl etherate; acetic acid; triethylamine; In methanol; dichloromethane;

DOI:10.1248/cpb.38.3347

Reference yield:

(R)-2-benzyloxy-3-trityloxy-propan-1-ol (91274-04-3) → (S)-2-O-benzyl-3-O-hexadecanoyl-1-O-<6-O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-gylcero-D-galacto-2-nonulopyranosylonate)-2,3,4-tri-O-acetyl-D-galactopyranosyl>glycerol (132929-03-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / triethylamine / CH₂Cl₂ / 15 h / Ambient temperature

2: 74.6 percent / 80percent AcOH / 1 h / 80 °C

3: molecular sieves 4A, BF₃-Et₂O / CH₂Cl₂ / 1) -10 deg C, 2 h, 2) room temperature, 15 h

With 4 A molecular sieve; boron trifluoride diethyl etherate; acetic acid; triethylamine; In dichloromethane;

DOI:10.1248/cpb.38.3347

upstream raw materials:

(2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-2-[(2R,3S,4S,5R)-3,4,5-triacetoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-ylmethoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

(S)-3-O-palmitoyl-2-O-benzylglycerol

benzyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside

(S)-2-(benzyloxy)-3-hydroxypropyl acetate

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